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Full text of "Screening tests against house flies with some derivatives of chrysanthemumic acid"

October 1953 E-865 



United States Department of Agriculture 

Agricultural Research Administration 

Bureau of Entomology and Plant Quarantine 



SCREENING TESTS AGAINST HOUSE FLIES WITH 
SOME DERIVATIVES OF CHRYSANTHEMUMIC ACID 

By Norman Mitlin, Nathan Green, W. A. Gersdorff, and M. S. Schechter 
Division of Insecticide Investigations 



Many materials related to allethrin that were prepared in this labo- 
ratory have shown no, or relatively little, toxicity when tested against 
house flies ( Musca domestica L.). Some of them were evaluated at the 
same tim.e as materials found to be more toxic and therefore were 
included in reports of these studies (Gersdorff 1, Gersdorff and Mitlin 
2, and LaForge et al. 3). Many, however, were tested in groups in 
which none of the materials showed promise for house fly control, and 
their evaluations were not reported. To make this information available 
it is assembled in this report. 

Materials 

These materials, although derivatives of chrysanthemumic acid, as 
is allethrin (dl-allethrolone esterified with a mixture of cis and trans 
dl- chrysanthemumic acids), were less closely related than those pre- 
viously reported. In their preparation the allethrolone portion of the 
molecule was replaced by widely differing compounds. These were of 
three types, alcohols, phenols, and amines. 

The esters of the alcohols and phenols were prepared by reacting 
them with a nnixture of cis and trans dl-chrysanthemumoyl chlorides in 
a hydrocarbon solvent in the presence of pyridine. 

About 0.1 mole of the anhydrous alcohol or phenol was placed in a 
500-ml. flask with 250 ml. of low-boiling petroleum ether and 0.12 mole 
of pyridine. If the alcohol or phenol did not dissolve, a small amount 
of dry benzene was added, although it was not considered necessary to 
have all the material in solution. The flask was placed under a reflux 
condenser and the acid chloride (0.105 mole) was added cautiously through 
the condenser while the flask was agitated. When the reaction subsided, 
the flask was stoppered and allowed to stand overnight. The next day 
water was added and the layers were separated. The upper layer wjis 
washed successively with 5 -percent sodium hydroxide solution, water. 



2 - 



10-percent hydi<" taoric acid solution, wait-r, ana lir.ally with saturated 
sodium chloride solution. The addition of a little ethyl ether was re- 
quired in a few instances to dissolve the product. After filtration 
through cotton, the solvents were removed on a steam bath and finally 
in a vacuum. The products were not purified. 

The amides were prepared in exactly the same fashion, an amine 
being used in place of the alcohol or phenol. 

In the case of dihydroxy compounds, 0.21 mole of the mixed cis 
and trans dl-chrysanthemumoyl chlorides was employed per 0.10 mole 
of alcohol or phenol in order to favor production of the diesters. The 
derivative of £-aminophenol, which is an ester as well as an amide, was 
prepared by employing a ratio of 0,21 mole of the mixed acid chlorides 
per 0.10 mole of p-aminophenol. 

The products were dissolved in refined kerosene or in mixtures of 
acetone and kerosene at different concentrations. 

The standard of comparison used was pyrethrins, in refined kerosene, 
at 1 mg. per milliliter. This spray caused 100-percent knockdown in all 
tests. 

Procedure 

Approximately 100 flies of 2 to 3:L.- **y/'^<^age were used in each test. 

Results 

The n^ortality and knockdown data are assembled in table^ 1. 
Since the materials were tested on many different populations of 
flies and hence with many different pyrethrum standards, comparison 
was made with pyrethrins at 1 mg. per milliliter, giving a range of 
16 to 25 percent mortality in one group and 26 to 35 percent in another. 

The compounds showed little toxicity at the concentrations tested. 
All were less than 0.06 as effective as pyrethrins, most of them less 
than 0.03. 

Literature Cited 
(1) Gersdorff. W. A. 

1949. Toxicity to house flies of synthetic compounds of the . rin 

type in relation ♦•^ -^f^mic.il struct' r.^ Jour. Ecor. .^.... 
42(3): 532-536. 

(2) and Mitlin, Norman 

1951. Relative toxicity of allethrin analogs to house flies. Jour. 
Econ. Ent. 44(1): 70-73. 
(3) LnK<^ri:e, F. H. . Gersdorff, W. A., Grren, Nathan, and Srherhtor, M.S. 

- ^1 va Qrg/aetails/cn ryesisag OOu n it 

V(;<); Mil 'AniK 



- 3- 



Table 1.- -Knockdown and mortality of house flies caused by derivatives of 
cis and trans dl-chrysanthemumic acids. All tests in duplicate unless 
otherwise noted. Concentration 32 mg. per milliliter. 



Materials 



Knockdown 
in 25 minutes 



Mortality 
in 24 hours 



Percent 
16 to 25 Percent Mortality With Pyrethrum Standard 
Esters of alcohols: 



Percent 



Butanol, 2 -ethyl- 
Cholesterol 
Cetyl alcohol 

Cyclohexanol, 2 -sec -butyl - 
Cyclohexanol, 2-cyclohexyl- 
Cyclohexanol, 4-cyclohexyl- 
Decyl alcohol 

Ethanol, 2-(p- tert -butylphenyl)- 
Ethanol, 2-cyclohexyl- 
Ethanol, l-(p-tolyl)-i/ 
Fenchyl alcohol 
Furfuryl alcohol 
3-Heptanol 
4-Heptanol^ 

4-Heptanol, 2,6-dimethyl- 
l,3-Hexa^ediol,2-ethyl- 
2,4-Hexadien-l -ol- 
Lauryl alcohol 

2,6-Octadien-4,5-diol (diester) 
Octyl alcohol / 

Phenethyl alcohol,dii^- dimethyl- 
Esters of phenols: 

Acetophenone, p-hydroxy- 
Benzophenone, p-hydroxy- 
Catechol (diester) 
o-Cresol,4-chloro- 
o-Cresol,6-chloro- 
p-Cresol-^ 



Hydroquinone (diester) 
Phenol,p-methoxy-^ 
8-Quinolinol-* / 

Resorcinol (diester)— 



L2^ 



4 
2 


2 
2 
5 


1 
1 

15 


86 

9 


1 




86 



1 

1 



3 

1 

26 

25 

25 

15 

1 



10 
3 
1 
5 
3 
4 
7 
3 
6 
2 
7 
6 
8 
2 
7 
6 
4 
9 
2 
5 
1 



4 
3 
4 
10 
4 
5 
7 
7 
2 
3 



-4- 



Table 1 .- -Continued 



Materials 



Knockdown 
in 25 minutes 



Mortality 
in 24 hours 



Percent 



Percent 



16 to 25 Percent Mortality With Pyrethrun^ Standard-- eowiiiiued 



Annides: 



Annylamine 

Amylamine, 1 -methyl- 

Butylamine 

Butylamine.l -methyl 

Carbazolei/ 

Diamylamine 

Dioctylamine , 

Diphenylamine-^ 

Heptylamine 

Isobutylamine 

Octylamine , 

Phenol.p-amino--^ 

Pyrrolidine 







1 

39 
1 

2 

2 

1 

58 



26 to 35 Percent Mortality With Pyrethrum Standard 



Esters of alcohols: 

Benzyl alcohol^-methyl- 

Benzyl alcohol^-(trichlorom ethyl) - 

1,3-Butanediol (diester) 

2,3-Butanediol (diester) 

2- Butanol,l, 1,1 -trichloro-2-methyl- 

Ethanol,2-bvitoxy- , 

Ethanol, 2 -( 2 -butoxyethoxy) -3r 

Ethanol,2-chloro- 

Ethanol,2-diethylamino- , 

Ethanol, 2 -dimethy lam ino — • 

Ethanol, 2-ethoxy-^ , 

Ethanol,2-(2-ethoxyethoxy)-^ 

E- • -^ - xy- 

t., .,„ ,_ ... 'Ik >\ vi>t!l(>V\) --3 

Ethanol, 2-phcn> 

Furfuryl alcohol, letrahydro 

3-Hexyne-2,5-diol,2,5-dimethyl 



1 
1 
3 
3 

3 
2 
2 
9 
4 
1 
2 
6 
1 

1 
1 



3 
4 
4 
8 
3 
2 
3 
4 
6 
5 
3 
3 
10 



16 
13 
1 
9 
6 
1 
4 
4 
2 

9 
I 

4 
3 
5 
3 
3 
4 



- 5 



Table 1. --Continued 



Materials 



Knockdown 
in 25 minutes 



Mortality 
in 24 hours 



26 to 35 Percent Mortality With Pyrethrum Standard- -continued 

Esters of alcohols (cont'd. ): 

4-Morpholineethanol— 4 9 

2-Nitropropanol,2-njethyl- 1 8 

Phenethyl alcohol, p-isopropyl- 1 6 

2-Propanol, 1-chloro- 3 17 

Propargyl alcohol 2 2 

2-Propen-l-ol,2-methyl- 3 9 

^-Terpeneol 5 5 

Esters of phenols: 

2 -Acetonaphthone,! -hydroxy- 89 2 

o-Cresol 1 3 

m-Cresol 6 8 

m-Cresol, amyl- 11 5 

p-Cresol-2-nitro- 2 13 

Eugenol 2 2 

cis -Isoeugenol 1 4 

trans -Isoeugenol 1 6 

Isoeugenol, benzyl- 3 7 

1-Naphthol 1 7 

2-Naphthol 1 4 

Phenol, p-tert -butyl- 3 

Phenol, o-chloro- 3 6 

Phenol,p-chloro- 1 5 

Phenol, m-methoxy- 42 7 

Thiophenol 1 13 

Vanillyl alcohol (diester) 8 

Amides: 

Allylamine , 42 4 

Morpholinei/ 51 9 

Piperidine^' 48 7 



y Acetone used as an auxiliary solvent. 
2/ Replicated three tinnes. 
3/ 16 mg. per milliliter. 



11 Uii 



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